Potassium Carbonate → HCID 15813212, compound

HRID 374887Notes

Reaction equation

HRID 374887 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12]C(=O)[N:10]([CH:14]([CH3:24])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:23])[CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Br[C:26](Br)([C:30](=[O:32])[CH3:31])[C:27](=[O:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:12])[CH2:9][NH:10][CH:14]([CH3:24])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]3[O:22][C:26]([C:30](=[O:32])[CH3:31])([C:27](=[O:29])[CH3:28])[O:23][C:18]=3[CH:17]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131689003,3-Dibromopentane-2,4-dioneHCID 156692045-(3-Chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone

Product 1

HCID 15813212HCID 15813212, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

One equivalent of 5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone, prepared by the procedure of U.S. Pat. No. 5,061,727, Example 1, is combined with 1.1 equivalents of 3,3-dibromo-2,4-pentanedione and 2.2 equivalents of powdered potassium carbonate in acetonitrile. The reaction mixture is stirred at room temperature for 48 hours, evaporated in vacuo and partitioned between methylene chloride and water. The organic layer is dried, filtered and evaporated in vacuo to give 5-(2-((2-(3-chlorophenyl)-2-hydroxyethyl)amino)propyl)-2,2-diacetyl-1,3-benzodioxole.

Workup

  1. customevaporated in vacuo
  2. custompartitioned between methylene chloride and water
  3. customThe organic layer is dried
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9c0e2da1bd314aebb80bdb61f0cabafb
Source dataset
uspto-grants-1996_01
Patent number
US05482971

Reaction notes

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